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Investigation of Novel Nanoparticles of Gallium Ferricyanide and Gallium Lawsonate As Potential Anticancer Agents, and Nanoparti

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Investigation of Novel Nanoparticles of Gallium Ferricyanide and Gallium Lawsonate As Potential Anticancer Agents, and Nanoparti Investigation of Novel Nanoparticles of Gallium Ferricyanide and Gallium Lawsonate as Potential Anticancer Agents, and Nanoparticles of Novel Bismuth Tetrathiotungstate as Promising CT Contrast Agent A Thesis submitted to Kent State University In partial fulfillment of the requirements for the degree of Master of Science Liu Yang August 2014 Thesis written by Liu Yang B.S. Kent State University, 2013 M.S. Kent State University, 2014 Approved by ___________________________________, Advisor, Committee member Dr. Songping Huang ___________________________________, Committee member Dr. Scott Bunge ___________________________________, Committee member Dr. Mietek Jaroniec Accepted by ___________________________________, Chair, Department of Chemistry Dr. Michael Tubergen ___________________________________, Dean, College of Arts and Sciences Dr. James L. Blank ii Table of Contents List of Figures..…………………………………………………………………........vii Acknowledgements ……………………………………………………………….….xi Chapter 1: Summary, Materials and Methods …..……………………………………1 1.1 Materials ………………………………………………………………….3 1.1.1 carboxymethyl reduced polysaccharide (CMRD) preparation….3 1.2 Methods …………………………………………………………………4 1.2.1 Atomic absorption spectroscopy (AA) …………………………4 1.2.2 Acid base treating method ……………………………………...4 1.2.3 Cell viability study ……………………………………………...5 i) MTT assay…………………………………………………..5 ii) Trypan blue assay ………………………………………….6 1.2.4 Dialysis …………………………………………………………6 1.2.5 Elementary analysis …………………………………………….7 1.2.6 Lyophilization …………………………………………………..7 iii 1.2.7 Kinetic study ……………………………………………………7 1.2.8 Thermal gravimetric analysis (TGA) ………………………..…8 1.2.9 Selectivity study ……………………………………….……..…8 1.2.10 Nanoparticle-surface conjugation of fluorescence dye molecules ...….………………………………………………………..9 1.2.11 X-ray attenuation measurements and CT phantom imaging…..9 1.2.12 Fourier transform infrared spectroscopy (FTIR)……………..10 1.2.13 Transmission electron microscopy (TEM) and energy dispersive X-ray (EDX)……………………………………………...10 Chapter 2: Novel Gallium Ferricyanide Nanoparticles as Potential Anticancer Drug …………………………………………………………………………………11 2.1 Abstract ………………………………………………………………….11 2.2 Introduction ……………………………………………………………...11 2.3 Synthesis and characterization of bulk gallium ferricyanide compound...19 2.3.1 Method A………………………………………………………19 2.3.2 Method B………………………………………………………21 2.3.3 Results and discussion of Ga[Fe(CN)6] bulk compound………25 iv 2.4 Synthesis and characterization of gallium ferricyanide nanoparticles…..27 2.4.1 Synthesis of gallium ferricyanide nanoparticles……………….27 2.4.2 Results and discussion ………………………………………...28 2.5 Conclusion……………………………………………………………….37 Chapter 3: Gallium Lawsonate Nanoparticles as Potential Anticancer Agent………38 3.1 Abstract …………………………………………………….……………38 3.2 Introduction ……………………………………………………………...38 3.3 Synthesis …………………………………………………….…………..43 3.4 Results and discussion ……………………………………….………….46 3.5 Conclusion ………………………………………………………………47 Chapter 4: Bismuth Tetrathiotungstate Nanoparticles as Potential Contrast Agent for Computed Tomography……………………………………………………………...48 4.1 Abstract ………………………………………………………………….48 4.2 Introduction ……………………………………………………………...48 4.3 Synthesis ………………………………………………………………...51 4.4 Results and discussion …………………………………………………..51 4.5 Conclusion ……………………………………………………………....56 v Chapter 5: References ……………………………………………………………….57 vi List of Figures Figure 1. Iron uptake through transferrin receptor (TfR). Fe 2+ is oxidized to Fe 3+ and bounded to transferrin protein (Tf). Diferric Tf binds to the receptor and internalized with clathrin coating through receptor mediated endocytosis. In the endosome, at lower pH, Fe3+ is released from transferrin protein and reduced back to Fe2+. Fe2+ can cross the membrane through ion channel and become available for other cellular process………………………………………………………………………………17 Figure 2. Ga3+ uptake mimicking the Fe3+ uptake pathway: Ga3+ crosses plasma membrane with the help of transferrin protein and transferrin receptor. Afterwards in the acidic endosome, Ga3+ is released from transferrin and enters cytoplasm………18 Figure 3. (up) Junction of endothelial cells in normal and healthy blood vessels is 5- 10 nm. NP (>10 nm) would pass through. (Bottom) Junction of endothelial cells in abnormal blood vessels is usually few hundred nanometers, NP(<100 nm) would leak out from abnormal blood vessels and target tumor tissue. ………………………….19 Figure 4. Fourier transform infrared spectroscopy (FT-IR) of the Ga[Fe(CN)6] bulk compound synthesized by method A………………………………………………...20 Figure 5. TGA of Ga[Fe(CN)6] bulk compound synthesized by method A. Weight lost below 200 ºC showed on the first drop on graph was due to the water lost, The vii second drop showed on graph above 200 ºC may due to cyanide lost. 21% weight loss was due to the water………………………………………………………………….21 Figure 6. TGA of Ga[Fe(CN)6] bulk compound synthesized by method B. Weight lost below 200 ºC showed on the first drop in the graph was due to the water lost. The second drop showed in the graph above 200 ºC may be due to cyanide lost. 21%weight loss was due to the water……………………………………………….23 Figure 7. FT-IR of Ga[Fe(CN)6] bulk compound synthesized by method B………24 Figure 8. The Fe(III) center donates electron through a d orbital to empty π*, an anti-bonding orbital of the CN ligand………………………………………………24 Figure 9. The formula used for calculating water molecules in crystal lattice. X represents the number of water molecules…………………………………………...25 Figure 10. FT-IR of gallium ferricyanide nanoparticles in comparison with gallium ferricyinde bulk compound and the CMRD polymer coating agent…………………29 Figure 11. Transmission electron microscopy (TEM) images of CMRD coated gallium ferricyanide nanoparticles with an average size of 25 nanometers…………29 Figure 12. Selectivity studies. Ga NPs undergo ion-exchange with 100 ppm of several M(II) ions for 24 hours showing that Fe(II) to be the most selective metal and Mn(II)/Mg(II) the least selective metals……………………………………………..30 Figure 13. Kinetic study. (Top) Fe2+ removal by Ga NPs vs. time. (Bottom) Within first 20 min, the removal of Fe2+ fits the pseudo-first order reaction………………...31 viii Figure 14. A: Preparation of fluorescence Ga NPs. B: Confocal microscopy images of T24 cells: (Top left) fluorescence image of cells incubated with dye-conjugated Ga NPs for 3 hours; (Top right) bright field images of cells incubated with dye conjugated Ga NPs for 3 hours; (lower left) florescence images of the cells untreated with NPs; (lower right) bright field image of the cells untreated with NPs……….33 Figure 15. Confocal microscopy images of HT-29 cells: (Top left) fluorescence image of cells incubated with dye-conjugated Ga NPs for 3 hours; (Top right) bright field images of cells incubated with dye conjugated Ga NPs for 3 hours; (lower left) florescence images of the cells untreated with NPs; (lower right) bright field image of the cells untreated with NPs…………………………………………………………34 Figure 16. Cell viability curve based on the MTT assay. Effect of Ga NPs on viability of HT-29 cells after 24 hour-incubation in comparison with the cell viability using Ga(NO3)3………………………………………………………………………35 Figure 17. Bright field light microscopic images. Various concentrations of Ga NPs used for incubating HT-29 cells for 24 hours. A: 1.58mM; B: 2.3mM; C: 3.15mM; D: 3.94mM; E: 4.73mM; F: 5.51mM; G: 6.3mM; H: NP-free control cells……………36 Figure 18. Structures of the oral gallium maltolate (right) and maltol……………..42 Figure 19. Structure of the oral KP46………………………………………………42 Figure 20. Structure of lawsone……………………………………………………..43 Figure 21. Synthetic scheme and proposed structure of gallium lawsonate………..44 ix Figure 22. Cell viability studies of Ga-lawsonate NPs on HT-29 Cells (Top) and T24 cells (Bottom) by MTT method …………………………………………………….45 Figure 23. Cell viability studies of Potassium lawsonate on T24 Cells……………46 Figure 24. (TOP) Transmission electron microscopy (TEM) image of Bi2(WS4)3 NPs on the 5-nm scale. (Bottom) Energy dispersive X-ray spectrum of Bi2(WS4)3 NPs; TEM analysis revealed that the nanoparticles are well-formed cubes and the size distribution appeared to be relatively wide, ranging from 2 to 10 nm……………….53 Figure 25: Fluorescence microscopic images of HeLa cells incubated with dye- labeled NPs for 3 hours: (right) Bright-field image, (left) confocal fluorescence microscopy image; Carboxyfluorescene dye was conjugated to the surfaces of the ethylenediamine-coated Bi2(WS4)3 NPs by the EDC-coupling reaction. Fluorescent signal in the cytoplasm of cells confirms the uptake of the NPs by the cells. Therefore these agents can serve as intracellular contrast agents……………………………….54 Figure 26. Histogram showing the viability of Hela cells in the presence of various amounts of Bi2(WS4)3 NPs after 24 hours of incubation as determined by the Trypan Blue exclusion method. ……………………………………………………………...55 Figure 27. Phantom images of Bi2(WS4)3 NPs at different concentrations………….55 Figure 28: The CT values vs. Bi(III) concentrations………………………………..56 x Acknowledgements I specially would like to thank Dr. Songping Huang for his years of patience and advice. Without his knowledge and assistance, I probably could not solve problems I met and keep the projects going. And I learned a lot from doing research these years. I would like to thank most senior lab member Vindya Perera for her help with TEM and confocal microscopy. And she also helped me to learn dialysis and lyophilization methods. I would like to thank Murthi S. Kandanapitiye
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